Photo Illustration by Sarah Rogers/The Daily Beast

Eight years ago, Kim Kardashian stepped into Trump Tower for an assessment meeting with Donald Trump. The subject of their evaluation? Rhinestone and sequin-embellished marketing displays for her perfume line—branded “The Voluptuous New Fragrance”—which was being promoted on a Season 10 episode of The Apprentice.

On Wednesday, Kim paid a visit to Trump’s new quarters for a wholly different type of tete-a-tete: this time to request a pardon for Alice Marie Johnson, a 62-year-old woman serving a life sentence for a first time drug offense.

While it’s unclear how receptive Trump was to Kardashian’s plea, there’s no shortage of precedent when it comes to his profoundly discerning take on her appearance.

“Does she have a good body? No. Does she have a fat ass? Absolutely,” he said in a 2013 interview with radio personality Howard Stern. Trump added, “At the word ‘Kim’ they’d say, ‘Wow, I don’t wanna go out with her.’”

During Kardashian’s pregnancy that same year, Trump, unprompted to speak about her looks, told a reporter, “She’s gotten a little bit large. I would say this, I don’t think you should dress like you weigh 120 pounds.”

In another interview with Stern a year later, Trump maintained his stance on Kardashian’s lower body. “It’s record setting,” he said. “In the old days, they’d say she’s got a bad body.”

All of this comes after Trump’s harsh 2009 firing of Kim’s sister Khloe Kardashian from Celebrity Apprentice. “She is a fat piglet. Why did we get the ugly Kardashian?” sources from the show have recalled Trump complaining at the time. In apparent reference to Kim, he reportedly added, “We can’t even get the hot one?”

Aesthetic preferences aside, two former reality television stars assembling at the White House to confer about criminal justice reform might seem like a bizarre scenario all on its own. But the summit takes on an added level of irony when considering what connected Trump and the Kardashians in the first place: Trump’s close friendship with O.J. Simpson, whom Kim’s father Robert Kardashian helped defend in court. Lest we forget, it was Simpson’s murder trial that thrust the Kardashian patriarch into the limelight to begin with, with the rest of his now-notorious family keeping up not far behind.

More than 10 years after O.J., who is also Kim’s godfather, was miraculously acquitted of murder, Kim Kardashian is advocating for a very different exoneration. Although Alice Johnson went to prison more than 21 years ago, Kardashian took up Johnson’s cause after coming across her story on Twitter earlier this year. In an interview this month, Kardashian expounded upon the discovery and her decision to support Johnson in requesting an official pardon.

“Where I’m at in my life right now, just like, to go and spend my money buying material things just doesn’t satisfy me the way that it used to,” Kardashian said. “To save someone’s life and do that once a year, then that would make my heart fuller.”